1,4-Butanedithiol

Chemical compound From Wikipedia, the free encyclopedia

1,4-Butanedithiol is an organosulfur compound with the formula HSCH2CH2CH2CH2SH. It is a malodorous, colorless liquid that is highly soluble in organic solvents. The compound has found applications in biodegradable polymers.[3]

Quick facts Names, Identifiers ...
1,4-Butanedithiol
Names
Preferred IUPAC name
Butane-1,4-dithiol[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.390 Edit this at Wikidata
EC Number
  • 214-728-3
UNII
  • Key: SMTOKHQOVJRXLK-UHFFFAOYSA-N
  • InChI=1S/C4H10S2/c5-3-1-2-4-6/h5-6H,1-4H2
  • C(CCS)CS
Properties
C4H10S2
Molar mass 122.24 g·mol−1
Appearance colorless liquid
Melting point −53.9 °C (−65.0 °F; 219.2 K)
Boiling point 195.5 °C (383.9 °F; 468.6 K)
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions

Alkylation with geminal dihalides gives 1,3-dithiepanes. Oxidation gives the cyclic disulfide 1,2-dithiane:[4]

HSCH2CH2CH2CH2SH + O → S2(CH2)4 + H2O

It forms self-assembled monolayers on gold.[5]

It is also used in polyadditions along with 1,4-butanediol to form sulfur-containing polyester and polyurethanes containing diisocyanate.[6][7][8] Several of these polymers are considered biodegradable and many of their components are sourced from non-petroleum oils.[9]

Related compounds

References

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